Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones.
Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones.
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DOI：
10.1039/c3ob41393d
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发表时间：
2013-08
影响因子：
3.2
通讯作者：
Feng-Lian Zhang;Yi‐Feng Wang;S. Chiba
中科院分区：
文献类型：
--
作者：
Feng-Lian Zhang;Yi‐Feng Wang;S. Chiba
通过将N-苄基酰胺肟与K3 PO 4在DMF中在60 °C下在O2气氛下加热经由苄基C-H氧化来实现1，2，4-恶二唑的简明合成。另一方面，在100 °C下，在DMSO中用Cs2 CO 3对N-苄基酰胺肟进行有氧处理可导致氧化骨架重排，以提供喹唑啉酮作为主要产物。这种正交产物选择性可通过反应温度的不同以及溶剂和无机碱的选择来实现。
Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60 °C under an O2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100 °C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.